68969-23-3Relevant academic research and scientific papers
A useful method for configuration assignement of vinyl sulfides; stereochemical reassessment of the radical addition of benzenethiol to alkynes
Benati, Luisa,Capella, Laura,Montevecchi, Pier Carlo,Spagnolo, Piero
, p. 1035 - 1038 (2007/10/02)
A comparative analysis of the 1H NMR spectra of (E)- and (Z)-phenyl and alkyl sulfides and their corresponding sulfones provides a useful method for establishing their configuration.Although by employing this method we generally confirm our previous configurational assignement for benzenethiol/alkyne adducts, those for (E)- and (Z)-3-(phenylsulfanyl)hex-3-ene and 4-phenylsulfanyl)oct-4-ene, are shown to have been assigned incorrectly.In the light of the present results it is concluded that radical addition of benzenethio to alkynes at 100 deg C generally proceeds with trans-selectivity.This conclusion is the reverse of our earlier claim for the effect that benzenethiol adds to terminal alkynes and alkylphenylacetylenes in a trans-stereoselective mode, but in a cis-stereoselective mode to dialkylacetylenes bearing (rather) bulky alkyl groups.
